Goodman also represented former San Diego Mayor Roger Hedgecock, who was convicted of accepting illegal campaign contributions and eventually forced to resign. Hedgecock was later cleared of all charges on appeal.

Goodman was a senior partner in the law firm of Goodman & Chesnoff.[5] Goodman currently serves as Of Counsel to Goodman Law Group, a Las Vegas law firm formed by his son, Ross C. Goodman.[6] Goodman was elected mayor of Las Vegas on June 8, 1999, receiving 32,765 (63.76 percent) votes while his opponent, then-Las Vegas City Councilman Arnie Adamsen, received 18,620 (36.24 percent). Goodman was re-elected to a second four-year term in 2003, defeating five opponents and receiving 29,356 (85.72 percent) of the votes. On April 3, 2007, he was re-elected to a third and final term with 26,845 votes (83.69 percent), again defeating five opponents. Las Vegas law prevents the mayor, who has been called the town's "most popular mayor",[7] from serving more than three terms.

On June 28, 1999, Goodman was the first mayor of Las Vegas to have his image placed on $5 and $25 casino chips issued by a Las Vegas casino. The two chips were issued by the Four Queens Hotel and Casino in Downtown Las Vegas. In 2006, the Four Queens put out a $200 Silver Strike with the likeness of Oscar on it.

Mayor Goodman was an invited celebrity photographer for the Playboy Cyber Club. He shot a topless pictorial of Miss January 2001 Irina Voronina for the website.

In 2002, he became a spokesman for Bombay Sapphire gin, receiving a $100,000 salary which was donated to charity, including $50,000 donated to The Meadows School, a private school in Las Vegas founded by his wife Carolyn.

In April 2003, he was re-elected for a second four-year term, winning 86% of all votes,[8] and becoming one of the most popular politicians elected to office in Las Vegas.[9]

In 2003, Las Vegas Review-Journal columnist John L. Smith wrote a book titled Of Rats and Men: Oscar Goodman's Life from Mob Mouthpiece to Mayor of Las Vegas, which chronicles Goodman's life, including 35 years spent defending notorious U.S. crime figures, including, among others, Meyer Lansky, Anthony "Tony The Ant" Spilotro and Frank "Lefty" Rosenthal (The last two were portrayed respectively, and under different names, in the film Casino by Joe Pesci and Robert De Niro).

In 2003, Goodman was voted the Least Effective Public Official in the Review-Journal's annual reader's poll.[10]

In recent years, Goodman has tried to get National Football League teams to Las Vegas. On April 24, 2006, he called the San Diego Chargers and asked if they would be interested in moving. Because of a contract, the city could not talk about a possible move. On January 4, 2007 he called again, since the team was not allowed to talk to other cities about a possible move. Again, Goodman was turned down "for the time being.[11] According to Mark Fabiani, the Chargers general counsel, Goodman is a longtime season ticket holder of the Chargers and a fan.[12]

He guest starred twice as himself on CSI in the episodes "Sqweegel" while defending Ann-Margret's character from being harassed by the LVPD and "Maid Man" CBS, first appearing at the opening of the Mob Museum, which was re-created for the show in advance of its opening.[13]

Goodman briefly entertained challenging presidential son Jack Carter for the Democratic nomination to run against incumbent Republican U.S. Senator John Ensign in 2006. However, on April 20, Goodman announced that he would not run but instead would run for a third term as mayor. After winning the mayoral election in 2007, Goodman, like his counterpart Michael Bloomberg in New York City, looked into a means to change the city charter to remove term limits.[14] In the absence of that change, Goodman fueled speculation that he might run as an Independent in the 2010 gubernatorial race against embattled incumbent, Republican Jim Gibbons, and the presumptive Democrat candidate, Rory Reid.[15] However, Goodman decided to drop out of the race for governor, citing his desire to stay close to his family and objections to moving to the capital Carson City.[16] Goodman has appeared interested in higher office and was the focus of a story (perhaps tongue-in-cheek) about being the first Jewish president of the United States by Las Vegas commentator Dayvid Figler.[17]

In February 2004, Robert Rose, an ethics watchdog, filed a complaint with the Nevada Commission on Ethics claiming that during the U.S. Conference of Mayors, Goodman handed out to fellow mayors, conference attendees and other political figures invitations to a cocktail party Goodman was hosting. Rose alleged that this was nothing more than the mayor abusing his power of office to help promote a business that is owned by his son, Ross Goodman, and Las Vegas Councilman Michael Mack. The Nevada Ethics Commission opened an investigation on April 14, 2004, and on May 13, 2004, the members of the commission found the mayor in ethics violations, although no fine was rendered. Goodman sued the commission and won; the commission's ruling was reversed by the court.

On September 16, 2004, Rose again filed a complaint with the Nevada Commission on Ethics, this time asking the commission to clarify Goodman's affiliation with his son Ross's law firm. In a statement, the mayor explained his name on the letterhead is a way of informing out of state law firms that Ross Goodman is his son. However, a person serving as an elected public official in Nevada may not have his name listed on a law firm letterhead, and Goodman removed his name under protest after several newspaper articles noted the infraction.[18]

On July 18, 2005, the Nevada Commission on Ethics concluded insufficient cause for a hearing and recommended the allegations be dismissed, clearing Goodman of the ethics complaint regarding his name listed as "Of Counsel" to Goodman Law Group.[19]

On September 11, 2007, the Supreme Court of Nevada ruled that Goodman did not violate any ethics laws during the 2004 cocktail party that he hosted on behalf of his son Ross C. Goodman.[20]

On March 3, 2005, Goodman spoke to a group of fourth-graders at Jo Mackey Elementary School. When asked what he would take with him if marooned on a desert island, the mayor replied, "A bottle of Bombay Sapphire Gin." When asked about his hobbies, the mayor named drinking Bombay Sapphire Gin as a favorite. Later, when asked to comment about his statements, Goodman was unapologetic: "I'm the George Washington of mayors. I can't tell a lie. If they didn't want the answer, the kid shouldn't have asked the question." This caused an outcry from parents whose children heard the remark, and school officials said the remark was inappropriate.[21][22]

In July 2006 the mayor criticized the Ubisoft game Tom Clancy's Rainbow Six: Vegas for its premise of terrorism in Las Vegas, because he thought it may tarnish the city's image. He stated, "It's based on a false premise.... It could be harmful economically, and it may be something that's not entitled to free speech (protection).... I will ask... whether or not we can stop it."[23] Publication of the game was not hindered.

Currently, prostitution is legal in Nevada only in rural counties with fewer than 400,000 residents, a requirement which excludes Clark County and the city of Las Vegas from allowing the practice. Mayor Goodman supports legalizing prostitution in the city's downtown area as a revenue generator and tool for revitalization,[24] although a majority of Nevadans polled in 2003 opposed the mayor's position.[25] Goodman's views on prostitution have been criticized by The New York Times columnist Bob Herbert,[26] as well as Las Vegas Sun columnist Jon Ralston.[27]